A practical free-radical approach to 1,4-dicarbonyl compounds

作者：Peralta Hernandez Eduardo; Ble Gonzalez Ever A; Gracia Medrano Bravo Victor A; Cordero Vargas Alejandro^*

来源：Tetrahedron, 2015, 71(15): 2234-2240.

DOI：10.1016/j.tet.2015.02.077

• Free radicals
• Radical-ionic sequence
• Vinyl acetates
• 1,4-Dicarbonyl compounds
• Octahydroindole

A practical radical/ionic sequence based on the addition of electrophilic radicals onto vinyl acetates, is described. The addition of such radicals, derived from commercially available iodoesthers, iodonitriles or iodoacetamides onto enol acetates generates the atom transfer adduct-a geminal halohydrine acetate which is unstable and therefore promotes the ionic elimination of the transferred iodine to thus regenerate the carbonyl compound. This simple protocol provides a broad variety of 1,4-dicarbonyl compounds (or equivalents), such as ketoaldehydes, ketoesters, ketonitriles, and formylnitriles.

• 出版日期2015-4-15